Sodium borohydride → 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidine

HRID 1271132Notes

Reaction equation

HRID 1271132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[C:17]([CH:18]=[O:19])=[C:16]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:15]=[C:14]([CH3:26])[N:13]=1)[CH2:6][CH2:5]2.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[N:7]([C:12]1[C:17]([CH2:18][OH:19])=[C:16]([NH:20][CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:15]=[C:14]([CH3:26])[N:13]=1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10178654HCID 10178654, compound

Product 1

HCID 101575044-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-formyl-2-methylpyrimidine, (50 mg, 0.13 mmol) was stirred with NaBH4 (7 mg, 0.2 mmol) in dry ethanol (2 mL) at 0° C. for 2 h. The reaction was partitioned between EtOAc (100 mL) and water (20 mL) and the EtOAc was washed with brine, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 40% EtOAc/hexanes to give the product, 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-hydroxymethyl-2-methylpyrimidine (40 mg, 80% yield).

Workup

  1. customThe reaction was partitioned between EtOAc (100 mL) and water (20 mL)
  2. washthe EtOAc was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on silica gel using 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-9f46dbe143174a4aa765d3594323e1c6
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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